Effect of Intramolecular Hydrogen Bonding on Thermolysis of Dioxetane: Unusual Instability of Bicyclic Dioxetanes Bearing a Hydroxynaphthyl Group with Vicinal Substitution Pattern

• Naoyuki Hoshiya

  Department of Chemistry, Kanagawa University

• Nobuko Watanabe

  Department of Chemistry, Kanagawa University

• Hisako K Ijuin

  Department of Chemistry, Kanagawa University

• Masakatsu Matsumoto

  Department of Chemistry, Kanagawa University

Abstract

Dioxetanes bearing a 1-hydroxynaphthalen-2-yl group 4(OH) or 2-hydroxynaphthalen-1-yl group 5(OH) were found to be significantly unstable thermally in contrast to their methoxynaphthyl-analogs 4(OME) and 5(OME). The marked instability of 4(OH) and 5(OH) was attributed to the intramolecular hydrogen bonding of a hydroxy group on the naphthalene ring.

Journal

• Chemistry Letters

  Chemistry Letters 36 (4), 516-517, 2007-03-03

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360283694087719808
• NII Article ID: 10018880908
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2007.516
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/36/4/516/55594148/cl.2007.516.pdf
• Data Source:
  • Crossref
  • CiNii Articles